Bromination of Saturated and Unsaturated Hydrocarbons
Dehydration of Sugar by Sulfuric Acid
Organic Synthesis With Familiar Materials
Oxidation of Primary, Secondary, Tertiary Alcohols
Underwater Fireworks: Chlorination of Acetylene
Differences in Miscibility of Organic Alcohols With Increasing Chain Length
Combustion of Cellulose Nitrate (Guncotton)
Different Smells of Carvone Isomers
Distinguishing Between HD and LD Polyethylene
Enviro-bond: Cleaning Oil Spills
Esterification Using a Dean-Stark Trap
IR Demonstration I – Atomic Coupling
IR Demonstrations II – Molecular Vibrations
IR Demonstration III – Molecular Vibrations
Making a Rubber Ball from Latex
Reaction Intermediates in Organic Chemistry
Reducing Sugars and Fehling’s Solution
Rod Climbing by a Polymer Solution
Superabsorbent Polyacrylate Gel
Aniline Hydrochloride-Formaldehyde Polymer
Relative Reactivity of Reducing Agents
Optical Activity of Racemic Mixtures With Limonene
Electrophilic Aromatic Substitution Reaction/EAS Reaction
Reactivity of Alkanes vs Aromatic Compounds
Relationship of Absorbed Light to Observed Color
Density and Miscibility of Liquids
Extraction of Copper Ions from Solution with Orform®
Gel Formation with Sodium Alginate and Calcium Chloride
Hydrolysis of T-butyl Chloride: A Lecture and Lab Experiment
Electrophilic Aromatic Substitution Reaction
Description: A set of four Petri dishes is filled with a mixture of TCNQ in Diglyme and placed on an overhead projector table and warmed with the lamp. Portions of Morpholine in Diglyme are added to the four petri dishes. The color of the solution in the dishes is dependent on the species in the liquid. The dye itself is a pale yellows, the first product, the TCNQ anion radical is green, and the first substitution product is dark blue. The third species the second Substitution product, is generated- by step addition of morpholine to the final petri dish, yielding a bright golden color.
Source: Novak, L.P, Brotero, P.P. El Seoud, O.A., Journal of Chemical Education
Year: 1989 Vol: 66 No.12 Page: 1040 – 1041
Keywords: EAS, Intermediate, Substitution, Organic Chemistry, Aromaticity, Conjugation, Delocalization
Rating: 
Hazards: Some
- Flammable liquids
- Reproductive capacity
- Acute toxicity- oral, dermal, inhalation
- Skin corrosion hazard
- Acute aquatic toxicity
- Severe eye damage
- Electric shock hazard
Effectiveness: Good
- Results are observable with guidance
- Good connection from demo to course material
- Mild effects are seen by audience
- Contrast between behavior of systems is notable
- Time to results is medium
- Moderate failure rate
Difficulty: High
- Use of sensitive reagents
- Multi-step procedures
- Demos that require training or extended practice to perform correctly
Safety Precautions:
- Eye protection required
- Nitrite gloves required
- Avoid exposure to dust, vapors, or mists
- Face shield recommended
- Lab coat recommended
- Perform in a well-ventilated
- Absorbent materials on hand
- ABC fire extinguisher required
- Sodium hydroxide or sodium hypochlorite on hand
- Use UL approved three-prong plug and outlet
Class: Types of Organic Reactions
Division: Organic, General
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